CN105175294B - Method for synthesizing sulfanilamide by using chlorobenzene as raw material - Google Patents
Method for synthesizing sulfanilamide by using chlorobenzene as raw material Download PDFInfo
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- CN105175294B CN105175294B CN201510538277.4A CN201510538277A CN105175294B CN 105175294 B CN105175294 B CN 105175294B CN 201510538277 A CN201510538277 A CN 201510538277A CN 105175294 B CN105175294 B CN 105175294B
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 title claims abstract description 44
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 15
- 229940124530 sulfonamide Drugs 0.000 title abstract description 7
- 239000002994 raw material Substances 0.000 title abstract description 4
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 12
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 10
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 9
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 238000010025 steaming Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- 229960004643 cupric oxide Drugs 0.000 claims description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 2
- 229940112669 cuprous oxide Drugs 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000001119 stannous chloride Substances 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 229940013123 stannous chloride Drugs 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000005915 ammonolysis reaction Methods 0.000 abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 238000005660 chlorination reaction Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000006277 sulfonation reaction Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 150000008422 chlorobenzenes Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RGAPVBWYXMTMAW-UHFFFAOYSA-N NC1=CC=C([S])C=C1 Chemical compound NC1=CC=C([S])C=C1 RGAPVBWYXMTMAW-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- SIQZJFKTROUNPI-UHFFFAOYSA-N 1-(hydroxymethyl)-5,5-dimethylhydantoin Chemical compound CC1(C)N(CO)C(=O)NC1=O SIQZJFKTROUNPI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UZXDEYWUHSZPLQ-UHFFFAOYSA-N ClC1=CC=CC=C1.[S] Chemical compound ClC1=CC=CC=C1.[S] UZXDEYWUHSZPLQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 235000019636 bitter flavor Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for synthesizing sulfanilamide by using chlorobenzene as a raw material. The method for synthesizing sulfanilamide by using chlorobenzene as the raw material is characterized by comprising the following steps: (a) adding ethylene dichloride and ammonium chloride, and dropwise adding chlorosulfonic acid into a reaction vessel, heating the reaction vessel to 50~60 DEG C and dropwise adding chlorobenzene to react continuously for 2~5h, and cooling the reaction vessel to 15~20 DEG C to obtain a first mixed liquid, wherein the mass ratio of the ethylene dichloride, the ammonium chloride, the chlorosulfonic acid and the chlorobenzene is (20~30):1:(20~30):(10~15); and (b) dropwise adding the first mixed liquid into ammonia water with concentration of 22~25%, after stirring and reacting the mixture for 0.5~1 hour, heating the mixture to 40~42 DEG C, continuously stirring and reacting the mixture for 1~2 h; then transferring the mixture to a high pressure reaction vessel, adding a catalyst, heating the mixture to 160~200 DEG C, carrying out reaction for 10~12 h; performing cooling, pressure relieving, steaming out the excess ammonia, adjusting the pH to 6.5~6.7, precipitating the solid, and after filtration and separation, performing drying, wherein the mass ratio of the ammonia water, the catalyst and the chlorobenzene is (120~150):1:(8~15). By using chlorosulfonic acid as sulfonation and sulfonyl chlorination reagents, chlorobenzene sulfonyl chloride can be synthesized in one step, and sulfanilamide can be obtained by ammonolysis. The materials directly enter into a high pressure vessel for ammonolysis without an intermediate separation process, so that the method is relatively short in route, easy to operate and high in total product yield.
Description
Technical field
The invention belongs to organic synthesis field, is related to a kind of synthetic method of P-aminobenzene-sulfonamide, and in particular to a kind of
With chlorobenzene as the method for Material synthesis P-aminobenzene-sulfonamide.
Background technology
P-aminobenzene-sulfonamide is white particle or powder crystal, odorless, mildly bitter flavor, 164.5 ~ 166.5 DEG C of fusing point.It
Cold water, ethanol, methyl alcohol, acetone is slightly soluble in, boiling water, glycerine, hydrochloric acid, potassium hydroxide and sodium hydroxide solution is soluble in, is not dissolved in
Benzene, chloroform, ether and petroleum ether.Medicine use can be pharmaceutically being done, is having inhibitory action to the growing multiplication of bacterium.
Peak lotus etc.（Volume 9 the 5th phase, Chemical Manufacture and technology in 2002）Report chlorobenzene method synthesis sulfanilamide (SN) new technology to grind
Study carefully, the method adopts chlorobenzene for raw material, sulfur trioxide has first synthesized p-chloro benzenesulfonamide, using SOCl as acylating reagent2Acyl
Chlorination synthesizes parachloroben-zenesulfonyl chloride, and ammoniacal liquor ammonolysis obtain p-chloro benzenesulfonamide, then obtain p-aminophenyl sulphur using high pressure ammonolysis
Acid amides, the method are the production methods of a relative clean.The method route of document report is longer, and total recovery is low, does not possess
Industrial value；And substantial amounts of accessory substance 4 is generated, 4 '-dichloro-benzenes sulfone is recrystallized using hot water in above-mentioned document report
Remove the impurity.
The content of the invention
The invention aims to overcome the deficiencies in the prior art and provide one kind with chlorobenzene as Material synthesis p-aminophenyl
The method of sulfonamide.
For reaching above-mentioned purpose, the technical solution used in the present invention is：One kind is with chlorobenzene as Material synthesis p-aminophenyl sulphur
The method of acid amides, it is characterised in that it comprises the following steps：
（a）Dichloroethanes, ammonium chloride is added in reactor and chlorosulfonic acid is added dropwise, instill chlorobenzene after being heated to 50 ~ 60 DEG C
Continue 2 ~ 5h of reaction, be cooled to 15 ~ 20 DEG C and obtain the first mixed liquor；The dichloroethanes, the ammonium chloride, the chlorosulfonic acid and institute
The mass ratio for stating chlorobenzene is 20 ~ 30：1：20~30：10~15；
（b）First mixed liquor is added drop-wise in the ammoniacal liquor that mass concentration is 22 ~ 25%, stirring reaction is after 0.5 ~ 1 hour
40 ~ 42 DEG C are warming up to, are continued 1 ~ 2h of stirring reaction, is subsequently transferred in autoclave, add catalyst, it is warming up to 160 ~
200 DEG C, 10 ~ 12h is reacted, cooling, pressure release steam unnecessary ammonia, adjust pH to 6.5 ~ 6.7, separate out solid, dry after being separated by filtration
It is dry；The ammoniacal liquor, the catalyst are 120 ~ 150 with the mass ratio of the chlorobenzene：1：8~15；The catalyst is chlorination
Copper, copper sulphate, stannous chloride, cupric oxide, cuprous oxide, cuprous iodide or cupric iodide；When from cuprous iodide or cupric iodide
Effect is more preferable, this is because the addition of iodide contributes to catalytic reaction, so as to further improve product efficiency.
Optimally, the step（b）In, the filtrate recovery after the ammonia for steaming and filtration.
As above-mentioned technical proposal is used, the present invention has following advantages compared with prior art：The present invention with chlorobenzene is
The method of Material synthesis P-aminobenzene-sulfonamide, using chlorosulfonic acid as sulfonation and chloride reagent, a step is completed to chlorobenzene sulphur
The synthesis of acyl chlorides, ammonolysis obtain parachloroben-zenesulfonyl chloride, are directly entered autoclave ammonolysis, without middle separation process, route phase
To short, processing ease, total yield of products is high；In the presence of using halogenated hydrocarbon solvent and hydrochloride, chlorobenzene is slowly added dropwise, can
To reduce the generation of accessory substance 4,4 '-dichloro-benzenes sulfone；The temperature of precise control reaction, the low chlorobenzene of temperature are enriched with systems, easily
Produce 4,4 '-dichloro-benzenes sulfone；Temperature is higher than 60 DEG C, can be further added by the probability that ortho position occurs sulfonating reaction, generates ortho position accessory substance,
It is difficult to remove.
Specific embodiment
Below will the present invention is described in detail by specific embodiment.
Embodiment 1
250kg dichloroethanes, 10.7kg ammonium chlorides is added in a kettle., and 265kg chlorosulfonic acids are subsequently added dropwise（15~30min
Drip off）, temperature is controlled at 55 DEG C, be slowly dropped into 112.5kg chlorobenzenes（4 ~ 5h is dripped off）, continuation reaction 4h is added, 15 DEG C are cooled to
Obtain the first mixed liquor；
Above-mentioned reactant is added to the ammoniacal liquor that 1500kg mass concentrations are 22wt% at 15 DEG C by control temperature of reaction kettle
In, finishing, stirring 1h is progressively warming up to 40 DEG C, continues stirring reaction 1h, is subsequently transferred in autoclave, fills ammonia to making
Ammonia saturation in solution, adds cupric iodide, is warming up to 160 DEG C, reacts 12h, and cooling, pressure release steam unnecessary ammonia, use watery hydrochloric acid
PH to 6.5 is adjusted, solid is separated out, P-aminobenzene-sulfonamide is dried to obtain in centrifugation（Total yield of products 97.5%, purity is
99.5%）.
Embodiment 2
200kg dichloroethanes, 10kg ammonium chlorides is added in a kettle., and 200kg chlorosulfonic acids are subsequently added dropwise（15 ~ 30min drops
It is complete）, temperature is controlled at 50 DEG C, be slowly dropped into 100kg chlorobenzenes（4 ~ 5h is dripped off）, add continuation reaction 2h, be cooled to 20 DEG C the
One mixed liquor；
Above-mentioned reactant is added to the ammoniacal liquor that 1200kg mass concentrations are 25wt% at 20 DEG C by control temperature of reaction kettle
In, finishing, stirring 0.5h is progressively warming up to 42 DEG C, continues stirring reaction 2h, is subsequently transferred in autoclave, fills ammonia extremely
Ammonia saturation in solution is made, copper sulphate is added, is warming up to 200 DEG C, react 10h, cooling, pressure release steam unnecessary ammonia, use dilute salt
Acid for adjusting pH separates out solid to 6.7, and P-aminobenzene-sulfonamide is dried to obtain in centrifugation（Total yield of products 95.6%, purity is
99.2%）.
Embodiment 3
300kg dichloroethanes, 10kg ammonium chlorides is added in a kettle., and 300kg chlorosulfonic acids are subsequently added dropwise（15 ~ 30min drops
It is complete）, temperature is controlled at 60 DEG C, be slowly dropped into 150kg chlorobenzenes（4 ~ 5h is dripped off）, add continuation reaction 5h, be cooled to 18 DEG C the
One mixed liquor；
Above-mentioned reactant is added to the ammoniacal liquor that 1300kg mass concentrations are 23wt% at 18 DEG C by control temperature of reaction kettle
In, finishing, stirring is progressively warming up to 40 DEG C for 40 minutes, continues stirring reaction 1.5h, is subsequently transferred in autoclave, fills ammonia
Gas adds copper chloride, is warming up to 180 DEG C to ammonia saturation in solution is made, and reacts 11h, and cooling, pressure release steam unnecessary ammonia, use
Watery hydrochloric acid adjusts pH to 6.6, separates out solid, and P-aminobenzene-sulfonamide is dried to obtain in centrifugation（Total yield of products 96%, purity is
99.0%）.
Above-described embodiment technology design only to illustrate the invention and feature, its object is to allow person skilled in the art
Scholar will appreciate that present disclosure and implement according to this, can not be limited the scope of the invention with this, all according to the present invention
Equivalence changes or modification that Spirit Essence is made, should all be included within the scope of the present invention.
Claims (2)
1. a kind of method with chlorobenzene as Material synthesis P-aminobenzene-sulfonamide, it is characterised in that it comprises the following steps：
（a）Dichloroethanes, ammonium chloride is added in reactor and chlorosulfonic acid is added dropwise, instill chlorobenzene and continue after being heated to 50 ~ 60 DEG C
2 ~ 5h of reaction, is cooled to 15 ~ 20 DEG C and obtains the first mixed liquor；The dichloroethanes, the ammonium chloride, the chlorosulfonic acid and the chlorine
The mass ratio of benzene is 20 ~ 30：1：20~30：10~15；
（b）First mixed liquor is added drop-wise in the ammoniacal liquor that mass concentration is 22 ~ 25%, stirring reaction heated up after 0.5 ~ 1 hour
To 40 ~ 42 DEG C, continue 1 ~ 2h of stirring reaction, be subsequently transferred in autoclave, add catalyst, be warming up to 160 ~ 200 DEG C,
10 ~ 12h of reaction, cooling, pressure release steam unnecessary ammonia, adjust pH to 6.5 ~ 6.7, separate out solid, are separated by filtration post-drying i.e.
Can；The ammoniacal liquor, the catalyst are 120 ~ 150 with the mass ratio of the chlorobenzene：1：8~15；The catalyst be copper chloride,
Copper sulphate, stannous chloride, cupric oxide, cuprous oxide, cuprous iodide or cupric iodide.
2. the method with chlorobenzene as Material synthesis P-aminobenzene-sulfonamide according to claim 1, it is characterised in that：It is described
Step（b）In, the filtrate recovery after the ammonia for steaming and filtration.
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| CN109456232A (en) * | 2018-12-17 | 2019-03-12 | 苏州华道生物药业股份有限公司 | A kind of preparation process of pair of ethyl beneznesulfonamide |
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| CN103483230B (en) * | 2013-09-09 | 2015-07-08 | 南通柏盛化工有限公司 | Preparation method of sulfanilamide |
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